Patent GB-825948-A (GB)
Title: Improvements in light-sensitive linear polymers
IPC: C07C59/64
Filed: 1956-05-25
Abstract: 4 - (g  - Hydroxypropoxy)benzaldehyde is prepared by reacting p-hydroxybenzaldehyde with 3-bromopropanol.  4 - Hydroxyethoxybenzal - 41 - bromoacetophenone is prepared by reacting 4-(b -hydroxy-ethoxy)benzaldehyde with p-bromoacetophenone.  4 - Hydroxyethoxybenzalanisalacetone is prepared by reacting 4-(b -hydroxyethoxy)benzaldehyde with anisalacetone. 4-Hydroxyethoxycinnamic acid is prepared by reacting 4-(b -hydroxyethoxy)benzaldehyde with malonic acid.  Ethyl 4-hydroxyethoxycinnamate is prepared by reacting 4-(b -hydroxyethoxy)benzaldehyde with ethyl hydrogen malonate.ALSO:Linear polymers comprise 20 to 100% by weight of recurring units of the form <FORM:0825948/IV (a)/1> or <FORM:0825948/IV (a)/2> wherein the benzene nucleus may contain alkyl or alkoxy substituents, R represents a styrene, vinyl ester, isopropenyl ester, alkyl acrylate, alkyl methacrylate, vinyl alkyl ether or ethylene unit, D represents either -OR1O-or -NH- where R1 is an alkylene group containing 1 to 4 carbon atoms, R2 represents a hydrogen atom, alkyl, nitro, cyano or -COOR4 group and A represents -OH, -R4, -OR4, -COOR4, -CH=CH-C6H4OR4, -C6H4-C6H5, -(CH=CH)n-C6H5 where n is 1 or 2, or <FORM:0825948/IV (a)/3> where m is 1 or 2 and X represents a hydrogen or halogen atom, -NO2, -CN, -R4, -OR4, -COOH, -COOR4, -CONH2 or <FORM:0825948/IV (a)/4> wherein R4 represents an alkyl group, the alkyl groups containing 1 to 4 carbon atoms.  The polymers may be prepared by reacting maleic anhydride interpolymers or polymethacrylic anhydride with hydroxyalkoxybenzaldehydes or aminobenzaldehydes, and thereafter reacting with compounds containing active methyl or methylene groups capable of reacting with aldehyde groups. Alternatively the aldehydes may be reacted with the compounds containing active methyl or methylene groups and the products reacted with the maleic anhydride or methacrylic anhydride polymers.  The reaction with the polymer may be effected in a liquid nitrogen base, e.g. pyridine.  Lists of aromatic aldehydes and compounds reactable therewith are given and examples describe the reaction of of styrene-maleic anhydride interpolymers, with (2) 4 - (b  - hydroxyethoxy) benzaldehyde and acetophenone or with 4-(b -hydroxyethoxy) benzalacetophenone, (3) 4-(lambda-hydroxypropoxy)-benzaldehyde and acetophenone or with 4-(g -hydroxypropoxy) benzalacetophenone, (6) 4-hydroxyethyoxybenzal - 41 - bromo - acetophenone, (8) 4-hydroxyethoxybenzalanisalacetone, (12) 4-hydroxyethoxycinnamic acid, (14) ethyl 4 - hydroxyethoxycinnamate, (16) 4-hydroxyethoxybenzal - 31 - nitroacetophenone, (18) 4 - hydroxyethoxy - a  - cyanocinnamic acid, (19) 4 - hydroxyethoxybenzal - 41 -phenylacetophenone, and (22) 3-aminobenzalacetophenone; polymethacrylic anhydride with (4) 4 - (lambda - hydroxypropoxy) benzaldehyde and acetophenone, (10) 4-hydroxyethoxybenzalanisalacetone, and (21) 4-(b -hydroxyethoxy) benzalpyruvic acid; and isopropenyl acetatemaleic anhydride interpolymers, with (9) 4-hydroxyethoxybenzalanisalacetone.  The products may be dissolved in solvents, e.g. acetone, dioxane, methyl ethyl ketone, pyridine, the monomethyl and monoethyl ethers of glycol and esters thereof, and chlorinated hydrocarbons, and coated on supports, e.g. of aluminium, zinc, copper, magnesium, paper, surface hydrolysed cellulose acetate or casein, and used in photographic and photomechanical reproduction.  They may be sensitized, e.g. with 2-benzoylmethylene - 1 - methyl - b  - naphthothiazoline, and, after exposure, images developed with a solvent, e.g. dilute ammonium hydroxide solution, aqueous acetone or methyl ethyl ketone.